Chicago

Chicago is the best American city that most people underestimate. World-class architecture, the deepest deep-dish pizza on the continent, a lakefront that runs 26 uninterrupted miles, and a live music scene rooted in the blues and house music. The L train connects everything; you never need a car. The architectural story here is genuinely unmatched in the United States — the Chicago Architecture Center runs river tours that explain why the downtown skyline looks the way it does, and the buildings themselves (Sullivan's Carson Pirie Scott, Mies's Lake Shore Drive apartments, Helmut Jahn's Thompson Center) are worth walking to. Millennium Park's Cloud Gate is the most-photographed sculpture in the country for a reason. The Art Institute houses one of the five best permanent collections in America. Food is one of Chicago's strongest cards. The West Loop (Fulton Market) has become one of the best restaurant neighborhoods in the country, with Alinea, Girl & The Goat, and Au Cheval all operating within blocks. The Chicago-style hot dog is the real thing — dragged through the garden, no ketchup. Giordano's and Lou Malnati's both make valid cases for best deep dish. The lakefront trail, Navy Pier, Hyde Park (home to the University of Chicago and the Obama Presidential Center under construction), Wrigleyville, and Andersonville round out a city with more depth than a weekend can handle.